Dichloromethane → HCID 22007443, compound

HRID 1740641Notes

Reaction equation

HRID 1740641 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]([C:18]3[CH:23]=[C:22]([C:24]4[C:33]5[C:28](=[CH:29][C:30]([O:36]CC6C=CC=CC=6)=[C:31]([O:34][CH3:35])[CH:32]=5)[CH:27]=[C:26]([CH2:44][OH:45])[C:25]=4[CH2:46][OH:47])[CH:21]=[CH:20][N:19]=3)[N:8]=2)[CH:2]=1.C(OC(=O)C)(=O)C.C(N(CC)CC)C.[Cl:62]CCl>>[ClH:62].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]([C:18]3[CH:23]=[C:22]([C:24]4[C:33]5[C:28](=[CH:29][C:30]([OH:36])=[C:31]([O:34][CH3:35])[CH:32]=5)[CH:27]=[C:26]([CH2:44][OH:45])[C:25]=4[CH2:46][OH:47])[CH:21]=[CH:20][N:19]=3)[N:8]=2)[CH:2]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10842384HCID 10842384, compound

Product 1

HCID 22007443HCID 22007443, compoundYield 25%

Procedure

To a solution of 1-[2-{4-(3-pyridyl)-1(2H)-phthalazinon-2-yl}-4-pyridyl]-2,3-bis(hydroxymethyl)-6-benzyloxy-7-methoxynaphthalene (0.73 g) in dichloromethane (10 ml) are added dropwise acetic anhydride (0.7 ml) and triethylamine (1.3 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. The mixture is diluted with dichloromethane, washed with water, dried, and concentrated under reduced pressure to remove the solvent. The residue is dissolved in acetic acid (50 ml) and thereto is added 10% palladium-carbon (0.1 g), and the mixture is subjected to medium-pressure catalytic hydrogenation at room temperature overnight with using a Parr reduction apparatus. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is dissolved in methanol (10 ml), and thereto is added sodium methoxide (0.2 g) under ice-cooling. The mixture is stirred at room temperature for three hours, and thereto is added diluted hydrochloric acid under ice-cooling. The mixture is concentrated under reduced pressure to remove the solvent. Water is added to the residue, and the mixture is extracted with dichloromethane. The extract is washed, dried, and concentrated under reduced pressure to remove the solvent. The residue is crystallized from ethyl acetate, and thereto is added 4M hydrogen chloride in ethyl acetate to give 1-[2-{4-(3-pyridyl)-1(2H)-phthalazinon-2-yl}-4-pyridyl]-2,3-bis(hydroxymethyl)-6-hydroxy-7-methoxynaphthalene hydrochloride (0.15 g, yield; 25%), which is listed in Table 12.

Workup

  1. temperaturecooling
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto remove the solvent
  6. dissolutionThe residue is dissolved in acetic acid (50 ml)
  7. additionis added 10% palladium-carbon (0.1 g)
  8. waitthe mixture is subjected to medium-pressure catalytic hydrogenation at room temperature overnight
  9. customThe catalyst is removed by filtration
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. dissolutionThe residue is dissolved in methanol (10 ml)
  12. additionis added sodium methoxide (0.2 g) under ice-
  13. temperaturecooling
  14. stirringThe mixture is stirred at room temperature for three hours
  15. additionis added diluted hydrochloric acid under ice-
  16. temperaturecooling
  17. concentrationThe mixture is concentrated under reduced pressure
  18. customto remove the solvent
  19. additionWater is added to the residue
  20. extractionthe mixture is extracted with dichloromethane
  21. washThe extract is washed
  22. customdried
  23. concentrationconcentrated under reduced pressure
  24. customto remove the solvent
  25. customThe residue is crystallized from ethyl acetate
  26. additionis added 4M hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-e69983a6ca074d4fa7b91afc8b95f67e
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

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